Sodium Chloride → Tasimelteon

反応式

[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[O:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[C:14]([C@@H:15]3[CH2:17][C@H:16]3[CH2:18][NH2:19])[C:9]=2[CH2:8][CH2:7]1.[Na+].[Cl-]>>[O:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[C:14]([C@@H:15]3[CH2:17][C@H:16]3[CH2:18][NH:19][C:1](=[O:4])[CH2:2][CH3:3])[C:9]=2[CH2:8][CH2:7]1

参加物

反応物 3

HCID 5234Sodium Chloride

HCID 62324Propionyl chloride

HCID 15858319((1R,2R)-2-(2,3-Dihydrobenzofuran-4-yl)cyclopropyl)methanamine

生成物 1

HCID 10220503Tasimelteon

実験手順

This compound was prepared similar to the above procedure using propionyl chloride and (-)-(trans)-2-(2,3-dihydrobenzofuran-4-yl)-cyclopropanemethanamine to give an oil that solidified upon standing to an off-white solid (61%, mp: 71°-72° C.). IR (NaCl Film): 3298, 1645, 1548, 1459, 1235 cm-1. [α]D25 : -17.3°; Anal. Calc'd for C15H19NO2 : C, 73.44; H, 7.87; N, 5.71; Found: C, 73.28; H, 7.68; N, 5.58.